{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,22]],"date-time":"2026-04-22T20:51:59Z","timestamp":1776891119731,"version":"3.51.2"},"reference-count":55,"publisher":"American Chemical Society (ACS)","issue":"3","license":[{"start":{"date-parts":[[2024,2,1]],"date-time":"2024-02-01T00:00:00Z","timestamp":1706745600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004489","name":"Mitacs","doi-asserted-by":"publisher","award":["FR70292"],"award-info":[{"award-number":["FR70292"]}],"id":[{"id":"10.13039\/501100004489","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Chem. Inf. Model."],"published-print":{"date-parts":[[2024,2,12]]},"DOI":"10.1021\/acs.jcim.3c01774","type":"journal-article","created":{"date-parts":[[2024,2,1]],"date-time":"2024-02-01T10:59:24Z","timestamp":1706785164000},"page":"697-711","source":"Crossref","is-referenced-by-count":31,"title":["Real-World Molecular Out-Of-Distribution: Specification and Investigation"],"prefix":"10.1021","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9841-9867","authenticated-orcid":true,"given":"Prudencio","family":"Tossou","sequence":"first","affiliation":[{"name":"Valence Labs, Montr\u00e9al, Qu\u00e9bec H2S3G9, Canada"},{"name":"Department of Computer Science and Software Engineering, Universit\u00e9 Laval, Montr\u00e9al, Qu\u00e9bec G1 V 0A6, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0006-2742-4817","authenticated-orcid":true,"given":"Cas","family":"Wognum","sequence":"additional","affiliation":[{"name":"Valence Labs, Montr\u00e9al, Qu\u00e9bec H2S3G9, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael","family":"Craig","sequence":"additional","affiliation":[{"name":"Valence Labs, Montr\u00e9al, Qu\u00e9bec H2S3G9, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hadrien","family":"Mary","sequence":"additional","affiliation":[{"name":"Valence Labs, Montr\u00e9al, Qu\u00e9bec H2S3G9, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emmanuel","family":"Noutahi","sequence":"additional","affiliation":[{"name":"Valence Labs, Montr\u00e9al, Qu\u00e9bec H2S3G9, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2024,2,1]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"publisher","DOI":"10.1016\/j.imu.2022.100880"},{"key":"ref2\/cit2","doi-asserted-by":"publisher","DOI":"10.34040\/IJCB.5.1.2015.71"},{"key":"ref3\/cit3","doi-asserted-by":"publisher","DOI":"10.1038\/d41573-022-00025-1"},{"key":"ref4\/cit4","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.13750"},{"key":"ref5\/cit5","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2018.01.039"},{"key":"ref6\/cit6","doi-asserted-by":"publisher","DOI":"10.1177\/026119290503300508"},{"key":"ref7\/cit7","unstructured":"OECD.\n                      Guidance Document on the Validation of (Quantitative)\nStructure-Activity\nRelationship [(Q)SAR] Models\n                      ; OECD, 2014, p 154."},{"key":"ref8\/cit8","doi-asserted-by":"publisher","DOI":"10.1063\/1.5023802"},{"key":"ref9\/cit9","unstructured":"Ji, Y.; Zhang, L.; Wu, J.; Wu, B.; Huang, L.K.; Xu, T.; Rong, Y.; Li, L.; Ren, J.; Xue, D.,  DrugOOD: Out-of-Distribution (OOD) Dataset Curator and Benchmark for AI-aided Drug Discovery - A Focus on Affinity Prediction Problems with Noise Annotations. 2022, arXiv preprint arXiv:2201.09637 (accessed Jan 24, 2022)."},{"key":"ref10\/cit10","doi-asserted-by":"publisher","DOI":"10.1021\/ci400084k"},{"key":"ref11\/cit11","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.9b00237"},{"key":"ref12\/cit12","volume-title":"Proceedings of Neural Information Processing Systems","author":"Huang K.","year":"2021"},{"key":"ref13\/cit13","unstructured":"Koh, P. W.;  WILDS: A Benchmark of in-the-Wild Distribution Shifts. 2020, CoRR, abs\/2012.07421 (accessed Dec 14, 2020)."},{"key":"ref14\/cit14","unstructured":"Muandet, K.; Balduzzi, D.; Sch\u00f6lkopf, B. Domain Generalization via Invariant Feature Representation\n                      International Conference on Machine Learning\n                      ; PMLR, 2013, pp 10\u201318."},{"key":"ref15\/cit15","first-page":"2178","volume":"24","author":"Blanchard G.","year":"2011","journal-title":"Adv. Neural Inf. Process. Syst."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"877","DOI":"10.1007\/978-3-030-71704-9_65","volume-title":"Advances in Data Science and Information Engineering","author":"Farahani A.","year":"2021"},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1039\/d2dd00146b"},{"key":"ref18\/cit18","doi-asserted-by":"publisher","DOI":"10.1109\/18.61115"},{"key":"ref19\/cit19","doi-asserted-by":"publisher","DOI":"10.1093\/bib\/bby065"},{"key":"ref20\/cit20","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkad404"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1038\/s41592-019-0666-6"},{"key":"ref22\/cit22","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.5b00238"},{"key":"ref23\/cit23","doi-asserted-by":"publisher","DOI":"10.1021\/ci600343x"},{"key":"ref24\/cit24","doi-asserted-by":"publisher","DOI":"10.1021\/acs.molpharmaceut.6b00471"},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1021\/jm101421d"},{"key":"ref26\/cit26","volume-title":"Experimental in Vitro DMPK and Physicochemical Data on a Set of Publicly Disclosed Compounds","author":"Wenlock M.","year":"2015"},{"key":"ref27\/cit27","doi-asserted-by":"publisher","DOI":"10.1038\/nbt.1581"},{"key":"ref28\/cit28","doi-asserted-by":"publisher","DOI":"10.1124\/dmd.108.020479"},{"key":"ref29\/cit29","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.5b00642"},{"key":"ref30\/cit30","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC02664A"},{"key":"ref31\/cit31","unstructured":"Han, K.; Lakshminarayanan, B.; Liu, J. Reliable Graph Neural Networks for Drug Discovery under Distributional Shift. 2021, arXiv preprint arXiv:2111.12951 (Nov 25, 2021)."},{"key":"ref32\/cit32","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.0c00915"},{"key":"ref33\/cit33","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gky1075"},{"key":"ref34\/cit34","doi-asserted-by":"publisher","DOI":"10.1038\/s42256-023-00740-3"},{"key":"ref35\/cit35","unstructured":"Shi, Y.; Zheng, S.; Ke, G.; Shen, Y.; You, J.; He, J.; Luo, S.; Liu, C.; He, D.; Liu, T.Y. Benchmarking Graphormer on Large-Scale Molecular Modeling Datasets. 2022, arXiv preprint arXiv:2203.04810 (accessed Mar 9, 2022)."},{"key":"ref36\/cit36","doi-asserted-by":"publisher","DOI":"10.1023\/A:1010933404324"},{"key":"ref37\/cit37","doi-asserted-by":"crossref","unstructured":"Rasmussen, C. E.\n                      Gaussian Processes in Machine Learning\n                      ; Summer school on machine learning, 2003, pp 63\u201371.","DOI":"10.1007\/978-3-540-28650-9_4"},{"key":"ref38\/cit38","first-page":"41","volume":"2","author":"Haykin S.","year":"2004","journal-title":"Neural Networks"},{"key":"ref39\/cit39","doi-asserted-by":"crossref","unstructured":"Sun, B.; Saenko, K.\n                      Deep CORAL: Correlation Alignment for Deep Domain Adaptation\n                      ; European conference on computer vision, 2016, pp 443\u2013450.","DOI":"10.1007\/978-3-319-49409-8_35"},{"key":"ref40\/cit40","first-page":"1","volume":"17","author":"Ganin Y.","year":"2016","journal-title":"J. Mach. Learn. Res."},{"key":"ref41\/cit41","unstructured":"Yan, S.; Song, H.; Li, N.; Zou, L.; Ren, L. Improve Unsupervised Domain Adaptation with Mixup Training. 2020, https:\/\/arxiv.org\/abs\/2001.00677 (accepted Jan 3, 2020)."},{"key":"ref42\/cit42","unstructured":"Blanchard, G.; Deshmukh, A. A.; Dogan, U.; Lee, G.; Scott, C. Domain Generalization by Marginal Transfer Learning. 2017. arXiv preprint arXiv:1711.07910 (accessed Mov 21, 2017)."},{"key":"ref43\/cit43","unstructured":"Krueger, D.; Caballero, E.; Jacobsen, J.H.; Zhang, A.; Binas, J.; Zhang, D.; Priol, R. L.; Courville, A. Out-of-Distribution Generalization via Risk Extrapolation (REx).\n                      Proceedings of the 38th International Conference on Machine Learning\n                      ; PMLR, 2020."},{"key":"ref44\/cit44","volume-title":"Invariance Principle Meets Information Bottleneck for Out-Of-Distribution Generalization","author":"Ahuja K.","year":"2021"},{"key":"ref45\/cit45","doi-asserted-by":"publisher","DOI":"10.1021\/ci010132r"},{"key":"ref46\/cit46","doi-asserted-by":"publisher","DOI":"10.1021\/ci100050t"},{"key":"ref47\/cit47","unstructured":"Landrum, G.\n                      RDKit: Open-Source Cheminformatics Software\n                      ; RDKit, 2016."},{"key":"ref48\/cit48","doi-asserted-by":"publisher","DOI":"10.1002\/qsar.200510159"},{"key":"ref49\/cit49","first-page":"28877","volume":"34","author":"Ying C.","year":"2021","journal-title":"Adv. Neural Inf. Process. Syst."},{"key":"ref50\/cit50","unstructured":"Hu, W.; Fey, M.; Ren, H.; Nakata, M.; Dong, Y.; Leskovec, J. OGB-LSC: A Large-Scale Challenge for Machine Learning on Graphs. 2021, arXiv preprint arXiv:2103.09430 (accessed Mar 17, 2021)."},{"key":"ref51\/cit51","unstructured":"Chithrananda, S.; Grand, G.; Ramsundar, B. ChemBERTa: Large-Scale Self-Supervised Pretraining for Molecular Property Prediction. 2020, arXiv preprint arXiv:2010.09885 (accessed Oct 19, 2020)."},{"key":"ref52\/cit52","unstructured":"Devlin, J.; Chang, M.W.; Lee, K.; Toutanova, K. Bert: Pre-training of Deep Bidirectional Transformers for Language Understanding. 2018, arXiv preprint arXiv:1810.04805 (accessed Oct 11, 2018)."},{"key":"ref53\/cit53","doi-asserted-by":"publisher","DOI":"10.1023\/B:MODI.0000006538.99122.00"},{"key":"ref54\/cit54","doi-asserted-by":"publisher","DOI":"10.1109\/TNN.2004.841784"},{"key":"ref55\/cit55","doi-asserted-by":"crossref","unstructured":"Akiba, T.; Sano, S.; Yanase, T.; Ohta, T.; Koyama, M. Optuna: A Next-Generation Hyperparameter Optimization Framework.\n                      Proceedings of the 25 Rd ACM SIGKDD International Conference on Knowledge Discovery and Data Mining\n                      ; Association for Computing Machinery, 2019.","DOI":"10.1145\/3292500.3330701"}],"container-title":["Journal of Chemical Information and Modeling"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jcim.3c01774","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jcim.3c01774","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,2,12]],"date-time":"2024-02-12T04:12:30Z","timestamp":1707711150000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.jcim.3c01774"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,2,1]]},"references-count":55,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2024,2,12]]}},"alternative-id":["10.1021\/acs.jcim.3c01774"],"URL":"https:\/\/doi.org\/10.1021\/acs.jcim.3c01774","relation":{"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv-2023-q11q4","asserted-by":"object"},{"id-type":"doi","id":"10.26434\/chemrxiv-2023-q11q4-v2","asserted-by":"object"}]},"ISSN":["1549-9596","1549-960X"],"issn-type":[{"value":"1549-9596","type":"print"},{"value":"1549-960X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,2,1]]}}}